# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Prof. Dr. Bernd Wrackmeyer' _publ_contact_author_address ;Anorganische Chemie I Universit\"atsstr. 30 95447 Bayreuth ; _publ_contact_author_email josef.breu@uni-bayreuth.de _publ_contact_author_phone '++49 921 552530' _publ_section_title ; Co-crystallisation of benzoic acid with sodium benzoate: Importance of stoichiometry ; loop_ _publ_author_name _publ_author_address C.Butterhof ;Anorganische Chemie I Universit\"at Bayreuth Universit\"atsstr. 30 95447 Bayreuth ; W.Milius ;Anorganische Chemie I Universit\"at Bayreuth Universit\"atsstr. 30 95447 Bayreuth ; J.Breu ;Anorganische Chemie I Universit\"at Bayreuth Universit\"atsstr. 30 95447 Bayreuth ; data_cb1 _database_code_depnum_ccdc_archive 'CCDC 865834' #TrackingRef 'CB1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H17 Na O6' _chemical_formula_weight 388.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.8941(12) _cell_length_b 14.565(3) _cell_length_c 22.299(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.30(3) _cell_angle_gamma 90.00 _cell_volume 1898.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS I' _diffrn_measurement_method 'phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12980 _diffrn_reflns_av_R_equivalents 0.0665 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3511 _reflns_number_gt 1867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS I' _computing_cell_refinement 'STOE CELL' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamnond Version 3.0e' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3511 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 0.803 _refine_ls_restrained_S_all 0.803 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Na1 Na 0.40621(14) 0.61478(5) 0.48724(3) 0.0565(2) Uani 1 1 d . . . O1 O 0.1409(3) 0.69643(10) 0.41852(6) 0.0584(4) Uani 1 1 d . . . O2 O -0.2097(2) 0.65908(10) 0.43679(6) 0.0619(4) Uani 1 1 d . . . H2 H -0.1402 0.6431 0.4693 0.093 Uiso 1 1 calc R . . O3 O 0.2916(2) 0.46721(9) 0.45348(6) 0.0512(4) Uani 1 1 d . . . O4 O -0.0151(2) 0.38038(9) 0.45927(6) 0.0537(4) Uani 1 1 d . . . O5 O 0.4843(3) 0.74654(10) 0.54715(7) 0.0679(4) Uani 1 1 d . . . O6 O 0.1627(3) 0.78425(11) 0.58331(8) 0.0780(5) Uani 1 1 d . . . H6A H 0.1205 0.7343 0.5691 0.117 Uiso 1 1 calc R . . C1 C -0.0633(4) 0.68961(13) 0.40144(8) 0.0460(5) Uani 1 1 d . . . C2 C -0.1648(3) 0.71381(12) 0.33871(8) 0.0435(5) Uani 1 1 d . . . C3 C -0.3900(4) 0.69474(14) 0.31655(9) 0.0540(5) Uani 1 1 d . . . H3 H -0.4874 0.6694 0.3418 0.065 Uiso 1 1 calc R . . C4 C -0.4695(4) 0.71348(16) 0.25683(10) 0.0632(6) Uani 1 1 d . . . H4 H -0.6206 0.7003 0.2419 0.076 Uiso 1 1 calc R . . C5 C -0.3278(4) 0.75130(15) 0.21934(10) 0.0640(6) Uani 1 1 d . . . H5 H -0.3826 0.7630 0.1791 0.077 Uiso 1 1 calc R . . C6 C -0.1053(4) 0.77187(15) 0.24101(10) 0.0633(6) Uani 1 1 d . . . H6 H -0.0093 0.7980 0.2157 0.076 Uiso 1 1 calc R . . C7 C -0.0252(4) 0.75341(14) 0.30068(9) 0.0555(5) Uani 1 1 d . . . H7 H 0.1252 0.7679 0.3155 0.067 Uiso 1 1 calc R . . C8 C 0.1041(3) 0.43484(12) 0.43070(8) 0.0422(5) Uani 1 1 d . . . C9 C 0.0120(3) 0.45852(12) 0.36672(8) 0.0415(4) Uani 1 1 d . . . C10 C -0.2114(3) 0.43824(13) 0.34264(9) 0.0502(5) Uani 1 1 d . . . H10 H -0.3094 0.4107 0.3668 0.060 Uiso 1 1 calc R . . C11 C -0.2893(4) 0.45869(15) 0.28292(9) 0.0578(6) Uani 1 1 d . . . H11 H -0.4390 0.4448 0.2672 0.069 Uiso 1 1 calc R . . C12 C -0.1451(4) 0.49969(15) 0.24671(9) 0.0616(6) Uani 1 1 d . . . H12 H -0.1975 0.5133 0.2066 0.074 Uiso 1 1 calc R . . C13 C 0.0753(4) 0.52031(15) 0.27008(9) 0.0602(6) Uani 1 1 d . . . H13 H 0.1726 0.5478 0.2457 0.072 Uiso 1 1 calc R . . C14 C 0.1539(4) 0.50050(13) 0.32968(9) 0.0510(5) Uani 1 1 d . . . H14 H 0.3033 0.5154 0.3452 0.061 Uiso 1 1 calc R . . C15 C 0.3687(4) 0.80322(15) 0.56888(9) 0.0534(5) Uani 1 1 d . . . C16 C 0.4408(4) 0.89977(13) 0.58155(9) 0.0513(5) Uani 1 1 d . . . C21 C 0.6427(4) 0.93092(15) 0.56293(10) 0.0629(6) Uani 1 1 d . . . H21 H 0.7370 0.8903 0.5455 0.075 Uiso 1 1 calc R . . C20 C 0.7045(5) 1.02231(17) 0.57017(11) 0.0733(7) Uani 1 1 d . . . H20 H 0.8399 1.0429 0.5574 0.088 Uiso 1 1 calc R . . C19 C 0.5663(6) 1.08288(17) 0.59615(12) 0.0815(8) Uani 1 1 d . . . H19 H 0.6062 1.1446 0.6000 0.098 Uiso 1 1 calc R . . C18 C 0.3696(6) 1.05179(16) 0.61626(13) 0.0835(8) Uani 1 1 d . . . H18 H 0.2791 1.0924 0.6350 0.100 Uiso 1 1 calc R . . C17 C 0.3041(4) 0.96058(15) 0.60898(10) 0.0669(6) Uani 1 1 d . . . H17 H 0.1697 0.9402 0.6224 0.080 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Na1 0.0560(5) 0.0468(4) 0.0616(5) -0.0059(4) -0.0127(4) 0.0034(4) O1 0.0440(10) 0.0699(10) 0.0587(9) 0.0103(7) -0.0037(7) -0.0024(7) O2 0.0488(10) 0.0900(11) 0.0458(8) 0.0123(7) 0.0022(7) -0.0035(8) O3 0.0469(9) 0.0472(7) 0.0555(8) -0.0021(6) -0.0092(6) -0.0049(6) O4 0.0549(10) 0.0580(8) 0.0464(8) 0.0052(7) 0.0000(6) -0.0115(7) O5 0.0633(11) 0.0561(9) 0.0836(11) -0.0223(8) 0.0066(8) 0.0014(8) O6 0.0719(13) 0.0592(10) 0.1068(13) -0.0190(9) 0.0263(10) -0.0118(8) C1 0.0461(15) 0.0434(11) 0.0484(12) 0.0001(9) 0.0056(10) 0.0011(9) C2 0.0448(13) 0.0384(10) 0.0463(11) 0.0006(8) 0.0023(9) 0.0020(8) C3 0.0461(14) 0.0620(13) 0.0532(13) 0.0054(10) 0.0036(10) -0.0048(10) C4 0.0495(15) 0.0761(15) 0.0603(14) 0.0027(12) -0.0079(11) -0.0062(11) C5 0.0717(18) 0.0678(15) 0.0492(13) 0.0114(11) -0.0060(12) 0.0030(12) C6 0.0626(18) 0.0700(14) 0.0569(14) 0.0170(11) 0.0055(11) -0.0067(11) C7 0.0488(15) 0.0577(13) 0.0586(14) 0.0085(10) 0.0016(10) -0.0051(9) C8 0.0435(14) 0.0379(10) 0.0442(11) -0.0055(8) 0.0020(9) 0.0011(9) C9 0.0435(13) 0.0385(10) 0.0421(10) -0.0038(8) 0.0040(8) -0.0007(8) C10 0.0442(14) 0.0568(12) 0.0490(12) -0.0020(9) 0.0037(9) -0.0013(9) C11 0.0480(15) 0.0710(14) 0.0514(13) -0.0038(11) -0.0055(10) 0.0050(10) C12 0.0756(19) 0.0662(14) 0.0411(12) 0.0028(10) -0.0002(11) 0.0073(12) C13 0.0703(18) 0.0609(13) 0.0508(13) 0.0040(10) 0.0130(11) -0.0065(11) C14 0.0481(14) 0.0520(12) 0.0529(13) -0.0045(9) 0.0067(10) -0.0053(9) C15 0.0536(16) 0.0533(13) 0.0516(12) -0.0040(10) 0.0000(10) 0.0005(11) C16 0.0529(15) 0.0473(11) 0.0510(11) -0.0035(9) -0.0038(9) -0.0012(10) C21 0.0597(17) 0.0628(14) 0.0633(14) -0.0026(11) -0.0037(11) 0.0006(11) C20 0.0686(19) 0.0719(17) 0.0739(16) 0.0094(13) -0.0125(13) -0.0186(14) C19 0.096(2) 0.0505(14) 0.0889(18) -0.0007(13) -0.0236(16) -0.0098(15) C18 0.100(2) 0.0531(15) 0.0934(19) -0.0183(13) -0.0046(16) 0.0085(14) C17 0.0697(18) 0.0569(14) 0.0730(15) -0.0112(12) 0.0051(12) 0.0027(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Na1 O3 2.3480(15) . ? Na1 O5 2.3502(16) . ? Na1 O1 2.3659(17) . ? Na1 O3 2.3976(16) 3_666 ? Na1 O4 2.7277(18) 3_566 ? Na1 O2 2.7304(18) 1_655 ? Na1 Na1 3.5447(16) 3_666 ? O1 C1 1.220(2) . ? O2 C1 1.318(2) . ? O2 Na1 2.7304(18) 1_455 ? O3 C8 1.248(2) . ? O3 Na1 2.3976(16) 3_666 ? O4 C8 1.282(2) . ? O4 Na1 2.7277(17) 3_566 ? O5 C15 1.210(2) . ? O6 C15 1.325(3) . ? C1 C2 1.492(3) . ? C2 C7 1.381(3) . ? C2 C3 1.384(3) . ? C3 C4 1.382(3) . ? C4 C5 1.370(3) . ? C5 C6 1.372(3) . ? C6 C7 1.381(3) . ? C8 C9 1.501(3) . ? C9 C10 1.389(3) . ? C9 C14 1.390(3) . ? C10 C11 1.385(3) . ? C11 C12 1.380(3) . ? C12 C13 1.370(3) . ? C13 C14 1.381(3) . ? C15 C16 1.486(3) . ? C16 C21 1.386(3) . ? C16 C17 1.390(3) . ? C21 C20 1.384(3) . ? C20 C19 1.377(4) . ? C19 C18 1.372(4) . ? C18 C17 1.387(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Na1 O5 163.19(7) . . ? O3 Na1 O1 96.48(6) . . ? O5 Na1 O1 91.34(6) . . ? O3 Na1 O3 83.35(5) . 3_666 ? O5 Na1 O3 90.86(6) . 3_666 ? O1 Na1 O3 172.30(6) . 3_666 ? O3 Na1 O4 86.51(5) . 3_566 ? O5 Na1 O4 81.12(6) . 3_566 ? O1 Na1 O4 75.20(5) . 3_566 ? O3 Na1 O4 112.44(5) 3_666 3_566 ? O3 Na1 O2 107.70(6) . 1_655 ? O5 Na1 O2 85.90(6) . 1_655 ? O1 Na1 O2 97.39(6) . 1_655 ? O3 Na1 O2 75.41(5) 3_666 1_655 ? O4 Na1 O2 164.83(5) 3_566 1_655 ? O3 Na1 Na1 42.21(4) . 3_666 ? O5 Na1 Na1 130.11(6) . 3_666 ? O1 Na1 Na1 138.16(5) . 3_666 ? O3 Na1 Na1 41.14(3) 3_666 3_666 ? O4 Na1 Na1 102.58(5) 3_566 3_666 ? O2 Na1 Na1 91.78(5) 1_655 3_666 ? C1 O1 Na1 134.92(13) . . ? C1 O2 Na1 165.12(13) . 1_455 ? C8 O3 Na1 132.84(12) . . ? C8 O3 Na1 126.39(12) . 3_666 ? Na1 O3 Na1 96.65(5) . 3_666 ? C8 O4 Na1 138.47(12) . 3_566 ? C15 O5 Na1 134.82(16) . . ? O1 C1 O2 122.41(18) . . ? O1 C1 C2 122.41(18) . . ? O2 C1 C2 115.17(18) . . ? C7 C2 C3 118.93(18) . . ? C7 C2 C1 118.36(19) . . ? C3 C2 C1 122.65(18) . . ? C4 C3 C2 119.8(2) . . ? C5 C4 C3 120.6(2) . . ? C4 C5 C6 120.2(2) . . ? C5 C6 C7 119.4(2) . . ? C6 C7 C2 121.0(2) . . ? O3 C8 O4 122.98(17) . . ? O3 C8 C9 119.63(17) . . ? O4 C8 C9 117.38(17) . . ? C10 C9 C14 118.44(18) . . ? C10 C9 C8 121.95(18) . . ? C14 C9 C8 119.60(18) . . ? C11 C10 C9 120.5(2) . . ? C12 C11 C10 120.2(2) . . ? C13 C12 C11 119.8(2) . . ? C12 C13 C14 120.4(2) . . ? C13 C14 C9 120.7(2) . . ? O5 C15 O6 122.4(2) . . ? O5 C15 C16 124.1(2) . . ? O6 C15 C16 113.58(19) . . ? C21 C16 C17 119.4(2) . . ? C21 C16 C15 119.24(19) . . ? C17 C16 C15 121.3(2) . . ? C20 C21 C16 120.2(2) . . ? C19 C20 C21 120.3(3) . . ? C18 C19 C20 119.7(2) . . ? C19 C18 C17 120.8(3) . . ? C18 C17 C16 119.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Na1 O1 C1 46.22(19) . . . . ? O5 Na1 O1 C1 -118.88(19) . . . . ? O3 Na1 O1 C1 134.5(4) 3_666 . . . ? O4 Na1 O1 C1 -38.42(18) 3_566 . . . ? O2 Na1 O1 C1 155.09(18) 1_655 . . . ? Na1 Na1 O1 C1 54.0(2) 3_666 . . . ? O5 Na1 O3 C8 86.8(3) . . . . ? O1 Na1 O3 C8 -30.43(18) . . . . ? O3 Na1 O3 C8 157.32(19) 3_666 . . . ? O4 Na1 O3 C8 44.24(17) 3_566 . . . ? O2 Na1 O3 C8 -130.35(17) 1_655 . . . ? Na1 Na1 O3 C8 157.32(19) 3_666 . . . ? O5 Na1 O3 Na1 -70.5(2) . . . 3_666 ? O1 Na1 O3 Na1 172.25(7) . . . 3_666 ? O3 Na1 O3 Na1 0.0 3_666 . . 3_666 ? O4 Na1 O3 Na1 -113.08(6) 3_566 . . 3_666 ? O2 Na1 O3 Na1 72.33(6) 1_655 . . 3_666 ? O3 Na1 O5 C15 -68.3(3) . . . . ? O1 Na1 O5 C15 49.6(2) . . . . ? O3 Na1 O5 C15 -137.8(2) 3_666 . . . ? O4 Na1 O5 C15 -25.2(2) 3_566 . . . ? O2 Na1 O5 C15 146.9(2) 1_655 . . . ? Na1 Na1 O5 C15 -124.2(2) 3_666 . . . ? Na1 O1 C1 O2 32.1(3) . . . . ? Na1 O1 C1 C2 -146.90(14) . . . . ? Na1 O2 C1 O1 165.4(4) 1_455 . . . ? Na1 O2 C1 C2 -15.6(6) 1_455 . . . ? O1 C1 C2 C7 -6.2(3) . . . . ? O2 C1 C2 C7 174.70(17) . . . . ? O1 C1 C2 C3 171.05(19) . . . . ? O2 C1 C2 C3 -8.0(3) . . . . ? C7 C2 C3 C4 1.5(3) . . . . ? C1 C2 C3 C4 -175.78(19) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? C4 C5 C6 C7 0.6(4) . . . . ? C5 C6 C7 C2 0.6(3) . . . . ? C3 C2 C7 C6 -1.6(3) . . . . ? C1 C2 C7 C6 175.76(19) . . . . ? Na1 O3 C8 O4 -108.05(19) . . . . ? Na1 O3 C8 O4 43.5(2) 3_666 . . . ? Na1 O3 C8 C9 72.9(2) . . . . ? Na1 O3 C8 C9 -135.49(14) 3_666 . . . ? Na1 O4 C8 O3 106.5(2) 3_566 . . . ? Na1 O4 C8 C9 -74.4(2) 3_566 . . . ? O3 C8 C9 C10 -168.37(18) . . . . ? O4 C8 C9 C10 12.5(3) . . . . ? O3 C8 C9 C14 12.8(3) . . . . ? O4 C8 C9 C14 -166.26(17) . . . . ? C14 C9 C10 C11 0.6(3) . . . . ? C8 C9 C10 C11 -178.19(18) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C12 C13 C14 C9 0.7(3) . . . . ? C10 C9 C14 C13 -0.9(3) . . . . ? C8 C9 C14 C13 177.92(18) . . . . ? Na1 O5 C15 O6 28.0(3) . . . . ? Na1 O5 C15 C16 -151.60(16) . . . . ? O5 C15 C16 C21 6.0(3) . . . . ? O6 C15 C16 C21 -173.56(18) . . . . ? O5 C15 C16 C17 -177.2(2) . . . . ? O6 C15 C16 C17 3.2(3) . . . . ? C17 C16 C21 C20 -1.7(3) . . . . ? C15 C16 C21 C20 175.12(19) . . . . ? C16 C21 C20 C19 0.3(3) . . . . ? C21 C20 C19 C18 1.6(4) . . . . ? C20 C19 C18 C17 -2.1(4) . . . . ? C19 C18 C17 C16 0.7(4) . . . . ? C21 C16 C17 C18 1.2(3) . . . . ? C15 C16 C17 C18 -175.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O4 0.82 1.77 2.5840(19) 174.7 3_566 O2 H2 O3 0.82 2.59 3.147(2) 126.0 3_566 O6 H6A O4 0.82 1.86 2.683(2) 176.6 3_566 _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.172 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.044